US3245948A - Vinyl halide polymers stabilized with basic lead salts of benzene polycarboxyalic acids - Google Patents
Vinyl halide polymers stabilized with basic lead salts of benzene polycarboxyalic acids Download PDFInfo
- Publication number
- US3245948A US3245948A US92766A US9276661A US3245948A US 3245948 A US3245948 A US 3245948A US 92766 A US92766 A US 92766A US 9276661 A US9276661 A US 9276661A US 3245948 A US3245948 A US 3245948A
- Authority
- US
- United States
- Prior art keywords
- lead
- basic lead
- benzene
- stabilizer
- salts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000003839 salts Chemical class 0.000 title claims description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims description 37
- 239000002253 acid Substances 0.000 title claims description 29
- -1 Vinyl halide Chemical class 0.000 title claims description 14
- 229920002554 vinyl polymer Polymers 0.000 title description 24
- 150000007513 acids Chemical class 0.000 title description 8
- 229920000642 polymer Polymers 0.000 title description 4
- 239000003381 stabilizer Substances 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 29
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- 229920005989 resin Polymers 0.000 description 26
- 239000011347 resin Substances 0.000 description 26
- 125000003118 aryl group Chemical group 0.000 description 25
- 125000005591 trimellitate group Chemical group 0.000 description 20
- 239000011342 resin composition Substances 0.000 description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 229920005646 polycarboxylate Polymers 0.000 description 11
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 10
- 239000004135 Bone phosphate Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- YJOMWQQKPKLUBO-UHFFFAOYSA-L lead(2+);phthalate Chemical compound [Pb+2].[O-]C(=O)C1=CC=CC=C1C([O-])=O YJOMWQQKPKLUBO-UHFFFAOYSA-L 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 5
- 238000013112 stability test Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000003801 milling Methods 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 230000009471 action Effects 0.000 description 3
- GCAIEATUVJFSMC-UHFFFAOYSA-N benzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1C(O)=O GCAIEATUVJFSMC-UHFFFAOYSA-N 0.000 description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 229910000464 lead oxide Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000004 White lead Inorganic materials 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 238000013494 PH determination Methods 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- QNSOHXTZPUMONC-UHFFFAOYSA-N benzene-1,2,3,4,5-pentacarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O QNSOHXTZPUMONC-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- OCWMFVJKFWXKNZ-UHFFFAOYSA-L lead(2+);oxygen(2-);sulfate Chemical compound [O-2].[O-2].[O-2].[Pb+2].[Pb+2].[Pb+2].[Pb+2].[O-]S([O-])(=O)=O OCWMFVJKFWXKNZ-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000005502 phase rule Effects 0.000 description 1
- 239000008029 phthalate plasticizer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/307—Monocyclic tricarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/313—Monocyclic acids containing more than three carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
Definitions
- Basic lead salts of various kinds have heretofore been employed as stabilizing agents for vinyl resin composi tions.
- Such basic lead salts may be mentioned, for example, dibasic lead phthalate, dibasic lead ph-osphite, basic carbonate White lead, basic silicate white lead and tribasic lead sulfate, among others. While such basic lead salts have been quite successful as stabilizing agents, and have gained wide popularity in the trade for this purpose, they nevertheless do not, nor does any stabilizer, confer complete immunity to heat, and there exists a continuing demand for still better stabilizers.
- this invention contemplates, as a new chemical compound, a basic lead salt of a 'benzenepolycarboxylic acid, said benzenepolycarboxylic acid having from 3 to 6 carboxyl groups present on the benzene ring.
- aromatic polycarboxylic acids having from 3 to, 6 carboxyl groups substituted on the benzene ring, form a series of basic lead salts.
- aromatic polycarboxylic acids capable of forming basic lead salts we mention trimellitic, trimesic, hemimel-liti-c, pyromelli-tic, mellophanic, prehnitic, benzene pentacarboxylic and :mellitic acids.
- the basic lead salt formed may be monobasic, dibasic, tribasic, tetrabasic or pentabasic and the salts may or may not have combined water. In either event good results can be realized.
- Methods for the preparation of the various aromatic polycarboxylic acids are known and constitute no part of the invention.
- the ratio of basic lead aromatic polyc-arboxylate to metal salt may vary greatly, but preferably for every 1 part of basic lead aromatic polycarboxylate there should be present from .01 to 10 parts of a metal salt.
- the invention may readily be prepared by adding water, acetic acid, and stoichiometric amounts of litharge, and trimellitic anhydride to a ball mill. The mill is sealed and rotated, with pH values determined at appropriate intervals. The completion of the formation of the basic lead salt is indicated by a constant pH value.
- the critical pH values of the reactions are: monobasic lead trimellitate, pH 5.4; tetrabasic lead trimellitate, pH 9.6.
- mixtures of the salts noted may be prepared.
- Other aromatic polycarboxylic acids mentioned above may be substituted and critical pH values may similarly be determined for the corresponding basic lead salts.
- mixtures of acids may be used resulting in mixed basic lead salts.
- a so-called solution catlyst such as acetic acid, nitric acid, or some other acid catalyst
- the amount of the catalytic agent employed may vary, the usual amount being from 0.10 to 0.15 pound per 100 pounds of litharge.
- Example I Monobasic lead trimellitate was prepared by placing 150 ml. of water, 4 ml. of 1% acetic acid, 35.61 gms. of litharge and 15.52 gms. of trimellitic anhydride, in that order, in a pebble mill. The mill was sealed and rotated at temperatures to 50 C., with pH values measured at appropriate intervals. After two milling operations of 24 hours at 25 C. and 20 hours at 50 C., the pH value was 5.4. After a third milling operation of 24 hours at 25 C., the pH remained constant at 5.4.
- the solid phase was then isolated by filtration and dried at a temperature of from 70 C. to C.
- the white product was composed of rounded crystals and analysis showed it to be 66.38% lead oxide, 27.57% trimellitic anhydride, and 6.05% water; its specific gravity was 3.71, and it had a mean refractive index of 1.84.
- Example II Tetrabasic lead trimellitate was prepared by placing 300 ml. of water, 8 ml. of 1% acetic acid, 81.46 gms. of litharge and 20.25 grns. of trimellitic anhydride in a pebble mill, in the order named, sealing and rotating at a temperature of 50 C.
- the pH was measured after three milling operations of 24, 18, and 20 hours with corresponding pH determinations of 9.2, 9.5 and 9.6. With the latter two successive pH values almost identical, the sol-id phase was then isolated by filtration and dried at a temperature of from 70 C. to 95 C.
- Mixtures of basic lead salts of trimellitic acid described above may be prepared in a similar manner by reacting the appropriate mole ratio of litharge to trimellitic anhydride.
- the di and tri salts are actually mixtures of the mono and tetra salts when microscopically examined.
- Example III parts of polyvinyl chloride resin were mixed with 50 parts of dioctyl phthalate plasticizer and 3 parts of monobasic lead trimellitate were added to the composition. Mixing and fluxing were accomplished in a fourminute cycle on a two-roll mill of the conventional type heated to a temperature of 300 F. The plastic composition was removed from the mill in the form of a sheet of 0.020 inch thickness.
- Example IV The procedure described in Example III was repeated, except that four samples, designated A, B, C, and D, were prepared, with varying formulations containing monobasic lead trimellitate alone and in conjunction with other stabilizers, and a control (sample A), containing no basic lead trimellitate.
- the four batches were milled as described in Example III, and portions of the plastic composition were withdrawn from the mill in the form of sheets of 0.020 and 0.040 inch thickness.
- the heat stability of each batch was determined by visual observation of the color of a 0.040 inch specimen after heating in a forced-circulation type oven for 25 minutes at 400 F.
- the volume resistivity was determined on the 0.020 inch specimens as described in the preceding example.
- the four samples designated A, B, C, and D, were prepared, with varying formulations containing monobasic lead trimellitate alone and in conjunction with other stabilizers, and a control (sample A), containing no basic lead trimellitate.
- the four batches were milled as described in
- a B o D 5 TABLE IV Polyvinyl chloride resin parts A B wt.) 100 100. 100 100 h. Di-Z-ethylhexyl phthalate, parts (wt. 59 50 50 50 50 Polyvinyl chloride resin 100 100 100 D basic lead .phthalate, parts (wt.) 3 1 1 10 Di-2-ethylhexyl phthalate 50 50 50 Monobasic lead trimellitate, parts 1 I Dibasic lead phthalate 3 (wt.) 3 2' 2 Tetrabasic lead trimesate 3 Barium stearate, partstwt.) Tribasic lead benzene tetracarboxyl 3 Volume resistivity at 70 C., 1n Volume resistivity at 70 C.
- Example V The procedure described in the preceding examples was employed to make experimental samples (B, C and D), employing respectively dibasic, tribasic and tetrabasic lead trimellitates, for comparison against a commerciallyacceptable control made with dibasic lead phthalate. All samples were processed in the manner previously described and tested for volume resistivity. The formulations and the results obtained are set forth in Table II:
- Example VI The procedures described in the foregoing examples were employed to prepare four samples illustrating the results achieved by use of basic lead trimellitate in combination with other stabilizers. The volume resistivity measurements and heat-stability tests were made in the same manner as described in the preceding examples. The formulations employed, and the results obtained, are set forth in Table III:
- Example VII The procedure described in Example I was employed in preparing tetrabasic lead trimesate and tribasic lead benzenetetracarboxylate. The volume resistivity measurements and heat-stability tests were made in the same Example VIII The procedure described in Example I was employed in preparing tribasic lead hemimellitate and tetrabasic lead trimesate. The volume resistivity measurements and heat stability tests were. made in the. same manner as described in the preceding examples, except that samples. were'exposed to a temperature of 375 F. for the heat stability test. The formulations employed and. the results obtained, are set forth in Table V:
- a 'B O- Polyvinyl chloride resin 100 100 Di-Z-ethylhexyl phthalata 50 50 50 Dibasiclead phthalate. 3 Tribasic lead hemimellitate 3 Tribasie lead trimesate 3 Volumelresistivity at 70 C. in 10 ohmcm- 3.8 5. 1 5. 5 Heat; stability Good Good V. Good Example IX Substituted polycarboxylic acids may be employed in preparing the basic lead salts of this invention. As a substituted polycarboxylic acid that can be utilized to form the basic lead polycarboxylate we mention 5-hydroxybenzene-l,2,4-trica rboxylic acid. This acid may be synthesized by a procedure essentially that of French Patent 816,718 and German Patent 686,908. The preparation of the basic lead salt may be done accordingly to the method described in the above examples.
- Tribasic lead S-hydroxy trimellitate was evaluated in the same manner as Example VIII, except that 5 parts of stabilizer was utilized in the composition.
- the formulations employed and the results obtained, are set forth in Table VI.
- coloring and'modifying agents may be present Without significantly afiecting the stabilization accomplished, and
- a resin composition comprising a vinyl halide resin and a stabilizer therefor, said stabilizer being a basic .lead salt of a benzene polycarboxylic acid, said benzene polycarboxylic acid having from 3 to: 6 cfarboxyl groups present on the benzene ring; and an electrical grade stabilizer; said stabilizers being present in the range of from 0.05% to 20% by weight based on the resin.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE614643D BE614643A (US06534493-20030318-C00166.png) | 1961-03-02 | ||
| NL275012D NL275012A (US06534493-20030318-C00166.png) | 1961-03-02 | ||
| NL136282D NL136282C (US06534493-20030318-C00166.png) | 1961-03-02 | ||
| US92766A US3245948A (en) | 1961-03-02 | 1961-03-02 | Vinyl halide polymers stabilized with basic lead salts of benzene polycarboxyalic acids |
| DE1962N0021196 DE1219223C2 (de) | 1961-03-02 | 1962-02-13 | Stabilisierung von Vinylhalogenidpolymerisaten und -mischpolymerisaten |
| CH193762A CH415044A (de) | 1961-03-02 | 1962-02-17 | Stabilisiertes Vinylhalogenidharz |
| AT977963A AT244941B (de) | 1961-03-02 | 1962-02-27 | Verfahren zur Herstellung von neuen basischen Bleisalzen aromatischer Polycarbonsäuren |
| FR889329A FR1316267A (fr) | 1961-03-02 | 1962-02-27 | Composition de résine vinylique stabilisée |
| DK97462AA DK102824C (da) | 1961-03-02 | 1962-03-01 | Stabilisator for vinylhalogenidformstoffer og fremgangsmåde til fremstilling af et basisk blysalt af en usubstitueret eller substitueret benzencarboxylsyre med fra 3 til 6 carboxylgrupper på benzenringen til anvendelse i stabilisatoren. |
| GB8073/62A GB979977A (en) | 1961-03-02 | 1962-03-01 | Basic lead salts of aromatic polycarboxylic acids and vinylhalide resin compositions containing such salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92766A US3245948A (en) | 1961-03-02 | 1961-03-02 | Vinyl halide polymers stabilized with basic lead salts of benzene polycarboxyalic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3245948A true US3245948A (en) | 1966-04-12 |
Family
ID=22235053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US92766A Expired - Lifetime US3245948A (en) | 1961-03-02 | 1961-03-02 | Vinyl halide polymers stabilized with basic lead salts of benzene polycarboxyalic acids |
Country Status (8)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3354110A (en) * | 1962-04-30 | 1967-11-21 | Standard Oil Co | Vinyl resins containing metal salts of benzene tricarboxylic acids |
| US3440213A (en) * | 1964-04-08 | 1969-04-22 | Nat Lead Co | Vinyl halide resins stabilized with tribasic lead isophthalate |
| US5475045A (en) * | 1994-06-09 | 1995-12-12 | Synthetic Products Company | Method and composition for reducing extractable heavy metals from vinyl halide resin compositions |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3244737A (en) * | 1962-04-30 | 1966-04-05 | Standard Oil Co | Dialkyl tin salts of aromatic polycarboxylates |
| DE4002988A1 (de) * | 1990-02-01 | 1991-08-14 | Baerlocher Chem | Basische calcium-aluminium-hydroxid-dicarboxylate, verfahren zu deren herstellung und deren verwendung |
| FR2722792B1 (fr) * | 1994-07-21 | 1996-09-06 | Ceca Sa | Compositions de type hydroxyde mixte d'aluminium et d'alcalino-terreux comme agents antichlore et anti-acides pour la stabilisation des resines thermoplastiques |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2275211A (en) * | 1938-01-17 | 1942-03-03 | Charles H Lewis | Process for liquid purification |
| US2330239A (en) * | 1940-11-25 | 1943-09-28 | Lubri Zol Corp | Lubricant |
| US2412784A (en) * | 1943-09-11 | 1946-12-17 | Nat Lead Co | Lead phthalates and process for preparing same |
| US2565171A (en) * | 1950-06-26 | 1951-08-21 | Allied Lab Inc | 2,2'-methylenebis (4-chlorophenoxyacetic acid) and a method for its production |
| US2922804A (en) * | 1956-11-23 | 1960-01-26 | Gen Electric | Basic lead p-nitrosophenolate |
| US2968642A (en) * | 1957-01-17 | 1961-01-17 | Lubrizol Corp | Stabilizers for polymeric compositions |
| US2970981A (en) * | 1958-04-10 | 1961-02-07 | Metal & Thermit Corp | Vinyl chloride resins comprising a stabilizing amount of a phosphine |
| US2985617A (en) * | 1955-09-02 | 1961-05-23 | Monsanto Chemicals | Stabilized polymer of 2 to 3 carbon atoms |
-
0
- NL NL136282D patent/NL136282C/xx active
- NL NL275012D patent/NL275012A/xx unknown
- BE BE614643D patent/BE614643A/xx unknown
-
1961
- 1961-03-02 US US92766A patent/US3245948A/en not_active Expired - Lifetime
-
1962
- 1962-02-13 DE DE1962N0021196 patent/DE1219223C2/de not_active Expired
- 1962-02-17 CH CH193762A patent/CH415044A/de unknown
- 1962-02-27 AT AT977963A patent/AT244941B/de active
- 1962-03-01 GB GB8073/62A patent/GB979977A/en not_active Expired
- 1962-03-01 DK DK97462AA patent/DK102824C/da active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2275211A (en) * | 1938-01-17 | 1942-03-03 | Charles H Lewis | Process for liquid purification |
| US2330239A (en) * | 1940-11-25 | 1943-09-28 | Lubri Zol Corp | Lubricant |
| US2412784A (en) * | 1943-09-11 | 1946-12-17 | Nat Lead Co | Lead phthalates and process for preparing same |
| US2565171A (en) * | 1950-06-26 | 1951-08-21 | Allied Lab Inc | 2,2'-methylenebis (4-chlorophenoxyacetic acid) and a method for its production |
| US2985617A (en) * | 1955-09-02 | 1961-05-23 | Monsanto Chemicals | Stabilized polymer of 2 to 3 carbon atoms |
| US2922804A (en) * | 1956-11-23 | 1960-01-26 | Gen Electric | Basic lead p-nitrosophenolate |
| US2968642A (en) * | 1957-01-17 | 1961-01-17 | Lubrizol Corp | Stabilizers for polymeric compositions |
| US2970981A (en) * | 1958-04-10 | 1961-02-07 | Metal & Thermit Corp | Vinyl chloride resins comprising a stabilizing amount of a phosphine |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3354110A (en) * | 1962-04-30 | 1967-11-21 | Standard Oil Co | Vinyl resins containing metal salts of benzene tricarboxylic acids |
| US3440213A (en) * | 1964-04-08 | 1969-04-22 | Nat Lead Co | Vinyl halide resins stabilized with tribasic lead isophthalate |
| US5475045A (en) * | 1994-06-09 | 1995-12-12 | Synthetic Products Company | Method and composition for reducing extractable heavy metals from vinyl halide resin compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1219223C2 (de) | 1973-11-15 |
| CH415044A (de) | 1966-06-15 |
| GB979977A (en) | 1965-01-06 |
| DE1219223B (de) | 1966-06-16 |
| AT244941B (de) | 1966-02-10 |
| BE614643A (US06534493-20030318-C00166.png) | |
| DK102824C (da) | 1965-10-11 |
| NL275012A (US06534493-20030318-C00166.png) | |
| NL136282C (US06534493-20030318-C00166.png) |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: ASSOCIATED LEAD INC., 2545 ARAMINGO AV4NUE, PHILDE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:NL INDUSTRIES, INC.;REEL/FRAME:003841/0028 Effective date: 19791017 |